CA2362554A1 - Utilisation de systemes 2-amino-thiazole polycycliques pour la production de medicaments destines a la prophylaxie ou au traitement de l'obesite - Google Patents
Utilisation de systemes 2-amino-thiazole polycycliques pour la production de medicaments destines a la prophylaxie ou au traitement de l'obesite Download PDFInfo
- Publication number
- CA2362554A1 CA2362554A1 CA002362554A CA2362554A CA2362554A1 CA 2362554 A1 CA2362554 A1 CA 2362554A1 CA 002362554 A CA002362554 A CA 002362554A CA 2362554 A CA2362554 A CA 2362554A CA 2362554 A1 CA2362554 A1 CA 2362554A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- phenyl
- ocf3
- substituted
- twice
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000011321 prophylaxis Methods 0.000 title claims abstract description 13
- 208000008589 Obesity Diseases 0.000 title claims abstract description 12
- 239000003814 drug Substances 0.000 title claims abstract description 12
- 235000020824 obesity Nutrition 0.000 title claims abstract description 12
- 238000011282 treatment Methods 0.000 title claims abstract description 12
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title abstract description 6
- 125000003367 polycyclic group Chemical group 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 132
- -1 biphenylyl Chemical group 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- 229910052794 bromium Inorganic materials 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
- 229910052731 fluorine Inorganic materials 0.000 claims description 40
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 37
- 229910052740 iodine Inorganic materials 0.000 claims description 33
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 32
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
- 230000001539 anorectic effect Effects 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 206010061428 decreased appetite Diseases 0.000 claims description 3
- 125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 claims description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical group C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 19
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000003826 tablet Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- CJXNKBIIMUOGBS-UHFFFAOYSA-N 5-(2,2,3,3,3-pentafluoropropoxy)-2,3-dihydroinden-1-one Chemical compound FC(F)(F)C(F)(F)COC1=CC=C2C(=O)CCC2=C1 CJXNKBIIMUOGBS-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XNTGHLJYUJLXQE-UHFFFAOYSA-N 2-bromo-5-chloro-2,3-dihydroinden-1-one Chemical compound ClC1=CC=C2C(=O)C(Br)CC2=C1 XNTGHLJYUJLXQE-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 230000001186 cumulative effect Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 210000004080 milk Anatomy 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYTWFOWLWWMFKO-UHFFFAOYSA-N (6-chloro-4h-indeno[1,2-d][1,3]thiazol-2-yl)cyanamide Chemical compound ClC1=CC=C2C(N=C(NC#N)S3)=C3CC2=C1 FYTWFOWLWWMFKO-UHFFFAOYSA-N 0.000 description 3
- CAJDYMAFIOUARK-UHFFFAOYSA-N 1-oxo-2,3-dihydroindene-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)CCC2=C1 CAJDYMAFIOUARK-UHFFFAOYSA-N 0.000 description 3
- QZPUXCULJWOZPL-UHFFFAOYSA-N 2-(dimethylamino)-4h-indeno[1,2-d][1,3]thiazole-6-carbonitrile;hydrobromide Chemical compound Br.N#CC1=CC=C2C(N=C(S3)N(C)C)=C3CC2=C1 QZPUXCULJWOZPL-UHFFFAOYSA-N 0.000 description 3
- CJMRJTDKLQFHNQ-UHFFFAOYSA-N 2-bromo-1-oxo-2,3-dihydroindene-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)C(Br)CC2=C1 CJMRJTDKLQFHNQ-UHFFFAOYSA-N 0.000 description 3
- JLJSWUFTNDGTFE-UHFFFAOYSA-N 2-bromo-5-(2,2,3,3,3-pentafluoropropoxy)-2,3-dihydroinden-1-one Chemical compound FC(F)(F)C(F)(F)COC1=CC=C2C(=O)C(Br)CC2=C1 JLJSWUFTNDGTFE-UHFFFAOYSA-N 0.000 description 3
- AUHASLVZMRLNKH-UHFFFAOYSA-N 2-chloro-5-pyridin-3-yl-2,3-dihydroinden-1-one Chemical compound C=1C=C2C(=O)C(Cl)CC2=CC=1C1=CC=CN=C1 AUHASLVZMRLNKH-UHFFFAOYSA-N 0.000 description 3
- FOUHAUHOOOZTAN-UHFFFAOYSA-N 5-(3-methylphenoxy)-2,3-dihydroinden-1-one Chemical compound CC1=CC=CC(OC=2C=C3CCC(=O)C3=CC=2)=C1 FOUHAUHOOOZTAN-UHFFFAOYSA-N 0.000 description 3
- QNSOPUXDEXJMIY-UHFFFAOYSA-N 5-pyridin-3-yl-2,3-dihydroinden-1-one Chemical compound C=1C=C2C(=O)CCC2=CC=1C1=CC=CN=C1 QNSOPUXDEXJMIY-UHFFFAOYSA-N 0.000 description 3
- ADBAWVWKQZKWBR-UHFFFAOYSA-N 6-(3-methylphenoxy)-4h-indeno[1,2-d][1,3]thiazol-2-amine;hydrochloride Chemical compound Cl.CC1=CC=CC(OC=2C=C3C(C=4N=C(N)SC=4C3)=CC=2)=C1 ADBAWVWKQZKWBR-UHFFFAOYSA-N 0.000 description 3
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
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- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
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- 150000007522 mineralic acids Chemical class 0.000 description 3
- SUIAMBGTEXPHDB-UHFFFAOYSA-N n-(6-chloro-4h-indeno[1,2-d][1,3]thiazol-2-yl)formamide Chemical compound ClC1=CC=C2C(N=C(NC=O)S3)=C3CC2=C1 SUIAMBGTEXPHDB-UHFFFAOYSA-N 0.000 description 3
- WRJSEADGCGEVFX-UHFFFAOYSA-N n-methyl-6-(2,2,3,3,3-pentafluoropropoxy)-4h-indeno[1,2-d][1,3]thiazol-2-amine;hydrochloride Chemical compound Cl.FC(F)(F)C(F)(F)COC1=CC=C2C(N=C(S3)NC)=C3CC2=C1 WRJSEADGCGEVFX-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
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- 239000000829 suppository Substances 0.000 description 3
- NCMWQYLZXFNASB-UHFFFAOYSA-N 2-(6-chloro-4h-indeno[1,2-d][1,3]thiazol-2-yl)-1-phenylguanidine Chemical compound C=1C(Cl)=CC=C(C=2N=3)C=1CC=2SC=3NC(=N)NC1=CC=CC=C1 NCMWQYLZXFNASB-UHFFFAOYSA-N 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 235000010489 acacia gum Nutrition 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000007966 viscous suspension Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 229940124024 weight reducing agent Drugs 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
L'invention concerne l'utilisation de systèmes 2-amino-thiazole polycycliques, ainsi que de leurs sels physiologiquement tolérés et de leurs dérivés physiologiquement fonctionnels. L'invention concerne l'utilisation de composés correspondant à la formule (I), dans laquelle les restes correspondent à la définition donnée, ainsi que de leurs sels physiologiquement tolérés et de leurs dérivés physiologiquement fonctionnels, pour la production d'un médicament servant à la prophylaxie ou au traitement de l'obésité.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19908537.4 | 1999-02-26 | ||
| DE19908537A DE19908537A1 (de) | 1999-02-26 | 1999-02-26 | Verwendung von polycyclischen 2-Amino-Thiazol Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas |
| PCT/EP2000/000925 WO2000051602A1 (fr) | 1999-02-26 | 2000-02-05 | Utilisation de systemes 2-amino-thiazole polycycliques pour la production de medicaments destines a la prophylaxie ou au traitement de l'obesite |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2362554A1 true CA2362554A1 (fr) | 2000-09-08 |
Family
ID=7899081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002362554A Abandoned CA2362554A1 (fr) | 1999-02-26 | 2000-02-05 | Utilisation de systemes 2-amino-thiazole polycycliques pour la production de medicaments destines a la prophylaxie ou au traitement de l'obesite |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6476059B1 (fr) |
| EP (1) | EP1173176B1 (fr) |
| JP (1) | JP4728483B2 (fr) |
| KR (1) | KR20020002394A (fr) |
| CN (1) | CN1161120C (fr) |
| AT (1) | ATE267597T1 (fr) |
| AU (1) | AU766295B2 (fr) |
| BR (1) | BR0008557A (fr) |
| CA (1) | CA2362554A1 (fr) |
| DE (2) | DE19908537A1 (fr) |
| DK (1) | DK1173176T3 (fr) |
| ES (1) | ES2218122T3 (fr) |
| HK (1) | HK1045809B (fr) |
| PT (1) | PT1173176E (fr) |
| WO (1) | WO2000051602A1 (fr) |
| ZA (1) | ZA200106199B (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19908538A1 (de) * | 1999-02-26 | 2000-08-31 | Aventis Pharma Gmbh | Polycyclische 2-Amino-Thiazol Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese Verbindungen |
| DK1183245T3 (da) * | 1999-04-22 | 2007-09-24 | Lundbeck & Co As H | Selektive NPY(Y5)-antagonister |
| WO2001064675A1 (fr) * | 2000-03-03 | 2001-09-07 | Novartis Ag | Thiazolamines condensees et leur utilisation comme antagonistes du neuropeptide y5 |
| US7732484B2 (en) * | 2000-08-01 | 2010-06-08 | University Of Virginia Patent Foundation | Use of selective adenosine A1 receptor allosteric enhancers to manipulate angiogenesis |
| EP1583530A4 (fr) * | 2002-01-16 | 2008-07-23 | Univ Virginia | Activateurs allosteriques 2-aminothiazoles des recepteurs de l'adenosine a1 |
| CA2530634A1 (fr) * | 2003-06-12 | 2004-12-23 | Menachem Rubinstein | Procedes permettant de traiter l'obesite et des troubles lies a l'obesite au moyen de composes contenant du tellure et du selenium |
| NZ552650A (en) * | 2004-08-05 | 2010-09-30 | Hoffmann La Roche | Substituted N-acyl-2-aminothiazoles |
| WO2006080406A1 (fr) * | 2005-01-28 | 2006-08-03 | Taisho Pharmaceutical Co., Ltd. | Composes tricycliques |
| RU2506267C2 (ru) * | 2008-03-31 | 2014-02-10 | Дженентек, Инк. | Бензопирановые и бензоксепиновые ингибиторы рi3k и их применение |
| AU2010299820A1 (en) | 2009-09-28 | 2012-04-19 | F. Hoffmann-La Roche Ag | Benzoxepin PI3K inhibitor compounds and methods of use |
| CA2772691C (fr) * | 2009-09-28 | 2017-10-03 | F. Hoffmann-La Roche Ag | Composes de benzoxazepine inhibiteurs de pi3k et leurs procedes d'utilisation |
| BR112013024122A2 (pt) | 2011-03-21 | 2019-09-24 | Hoffmann La Roche | compostos de benzoxazepina seletivos para p110 delta pi3k e métodos de uso |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3507868A (en) * | 1968-10-21 | 1970-04-21 | Sandoz Ag | Imidazo(2,1-b)thiazoles and thiazolo(3,2-a)pyrimidines |
| DE2640358A1 (de) * | 1976-09-08 | 1978-03-16 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| JPS5334471A (en) * | 1976-09-10 | 1978-03-31 | Toshiba Corp | Manufacture for semiconductor device |
| CA1292226C (fr) * | 1986-01-16 | 1991-11-19 | Terumi Hachiya | Derived'indenothiazole, et sa preparation |
| IE68593B1 (en) * | 1989-12-06 | 1996-06-26 | Sanofi Sa | Heterocyclic substituted acylaminothiazoles their preparation and pharmaceutical compositions containing them |
| DE19831878C2 (de) * | 1998-07-17 | 2001-05-17 | Aventis Pharma Gmbh | Polycyclische Thiazolidin-2-yliden Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE19908538A1 (de) * | 1999-02-26 | 2000-08-31 | Aventis Pharma Gmbh | Polycyclische 2-Amino-Thiazol Systeme, Verfahren zu ihrer Herstellung und Arzneimittel enthaltend diese Verbindungen |
-
1999
- 1999-02-26 DE DE19908537A patent/DE19908537A1/de not_active Withdrawn
-
2000
- 2000-02-05 JP JP2000602070A patent/JP4728483B2/ja not_active Expired - Fee Related
- 2000-02-05 BR BR0008557-0A patent/BR0008557A/pt not_active IP Right Cessation
- 2000-02-05 EP EP00905028A patent/EP1173176B1/fr not_active Expired - Lifetime
- 2000-02-05 KR KR1020017010840A patent/KR20020002394A/ko not_active Ceased
- 2000-02-05 AU AU26703/00A patent/AU766295B2/en not_active Ceased
- 2000-02-05 HK HK02107056.4A patent/HK1045809B/zh not_active IP Right Cessation
- 2000-02-05 CN CNB008042209A patent/CN1161120C/zh not_active Expired - Fee Related
- 2000-02-05 PT PT00905028T patent/PT1173176E/pt unknown
- 2000-02-05 DE DE50006603T patent/DE50006603D1/de not_active Expired - Lifetime
- 2000-02-05 AT AT00905028T patent/ATE267597T1/de not_active IP Right Cessation
- 2000-02-05 ES ES00905028T patent/ES2218122T3/es not_active Expired - Lifetime
- 2000-02-05 WO PCT/EP2000/000925 patent/WO2000051602A1/fr not_active Ceased
- 2000-02-05 DK DK00905028T patent/DK1173176T3/da active
- 2000-02-05 CA CA002362554A patent/CA2362554A1/fr not_active Abandoned
- 2000-02-10 US US09/501,209 patent/US6476059B1/en not_active Expired - Lifetime
-
2001
- 2001-07-27 ZA ZA200106199A patent/ZA200106199B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR0008557A (pt) | 2001-12-18 |
| DK1173176T3 (da) | 2004-09-27 |
| ZA200106199B (en) | 2002-03-06 |
| CN1161120C (zh) | 2004-08-11 |
| AU2670300A (en) | 2000-09-21 |
| DE50006603D1 (de) | 2004-07-01 |
| ES2218122T3 (es) | 2004-11-16 |
| CN1349404A (zh) | 2002-05-15 |
| HK1045809B (zh) | 2005-04-22 |
| US6476059B1 (en) | 2002-11-05 |
| JP4728483B2 (ja) | 2011-07-20 |
| PT1173176E (pt) | 2004-09-30 |
| EP1173176B1 (fr) | 2004-05-26 |
| DE19908537A1 (de) | 2000-08-31 |
| KR20020002394A (ko) | 2002-01-09 |
| WO2000051602A1 (fr) | 2000-09-08 |
| EP1173176A1 (fr) | 2002-01-23 |
| HK1045809A1 (en) | 2002-12-13 |
| JP2002538117A (ja) | 2002-11-12 |
| ATE267597T1 (de) | 2004-06-15 |
| AU766295B2 (en) | 2003-10-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |